5 Can’t-Miss Chicago Festivals to Put on Your Calendar

From family-friendly music festivals to food fests serving up delicious fare, here are five Chicago area festivals to check out this summer.

Pride Month

Throughout June 

This year, Pride Month is jam-packed with nearly a hundred different political, social, and cultural hap­penings reflecting the important influence of Chicago’s LGBTQ+ community. Chicago’s Boystown was America’s first recognized gay neighborhood, and it remains the epicenter for many of these upcoming events. The Windy City has long embraced the celebration of gay culture and community known as Pride Week, starting with Pride Fest (June 22-23), then Pride in the Park (June 29), and wrapping up with the Chicago Pride Parade on June 30. Always a summer highlight, this year’s Pride Week has particular resonance as Chicago’s LGBTQ+ community pays homage to the 50th anniversary of Stonewall, a pivotal event in gay history. Close to 100,000 people are expected to attend Pride Fest, a two-day street festival held at Halsted Street and Addison, while the 50th Annual Pride Parade will kick off at noon on Sunday, June 30. More than a million revel­ers are expected to line the streets as the joyful, rainbow-laden parade makes its way through the Uptown and Lakeview neighborhoods.

Chicago Blues Festival

June 7-9

Chicago Festivals: Chicago Blues Festival
Photo courtesy of City of Chicago.

As usual, Millennium Park will be rocking and rolling all summer long. From June 7-9, don’t miss the Chicago Blues Festival — the world’s largest free blues festival and the largest of Chicago’s music festivals. Music begins every day at 11 a.m. and headliners take the stage from 5-9 p.m. at the Jay Pritzker Pavilion.

Ribfest Chicago

June 9

The intersection of Lincoln Avenue, Irving Park, and Damen in Northcenter never smelled so delicious! Get summer rolling with this celebration of ribs, whether dry-rubbed, wet-brined, or smoked, as both local and national restaurants vie for the coveted title of Best Ribs. Music, drinks, and more are also on the docket.

Winnetka Music Festival

June 21-22

Chicago Festivals: Winnetka Music Festival
Photo by Scott Edwards.

Our friends over at Val’s List are bringing the jams to the North Shore at the 3rd Annual Winnetka Music Festival June 21-22. Val Haller, contemporary music savant, curates an eclectic and exciting mix of emerging artists and unique live events. Ride-share, bike, or train it to the heart of downtown Winnetka and spend the day wandering between festival stages and food trucks, or hit up one of the many nearby restaurants. Great for the whole family!

Windy City Smokeout

July 12-14

More than 20 acclaimed pitmasters from around the country will descend en masse on Chicago for this annual summer barbecue festival taking place outside the United Center. Combine that with two dozen craft brewers and 18 country music acts and you’ve got yourself the ultimate summer party, Chicago-style.


Julie Chernoff, Make It Better’s dining editor since its inception in 2007, graduated from Yale University with a degree in English — which she speaks fluently — and added a professional chef’s degree from the California Culinary Academy. She has worked for Boz Scaggs, Rick Bayless, and Wolfgang Puck (not all at the same time); and counts Northlight Theatre and Les Dames d’Escoffier International as two of her favorite nonprofits.